(2R,3S,4R,6R)-7-(tert-butyldiphenylsilyloxy)-2,3,6-trihydroxy-4-methylheptanoic acid ethyl ester

Base Information

• Chemical Name: (2R,3S,4R,6R)-7-(tert-butyldiphenylsilyloxy)-2,3,6-trihydroxy-4-methylheptanoic acid ethyl ester
• CAS No.: 922516-85-6
• Molecular Formula: C₂₆H₃₈O₆Si
• Molecular Weight: 474.67
• Mol file: 922516-85-6.mol

Synonyms:(2R,3S,4R,6R)-7-(tert-butyldiphenylsilyloxy)-2,3,6-trihydroxy-4-methylheptanoic acid ethyl ester

Chemical Property of (2R,3S,4R,6R)-7-(tert-butyldiphenylsilyloxy)-2,3,6-trihydroxy-4-methylheptanoic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,4R,6R)-7-(tert-butyldiphenylsilyloxy)-2,3,6-trihydroxy-4-methylheptanoic acid ethyl ester

There total 1 articles about (2R,3S,4R,6R)-7-(tert-butyldiphenylsilyloxy)-2,3,6-trihydroxy-4-methylheptanoic acid ethyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

(4R,6R)-7-(tert-butyldiphenylsilyloxy)-6-hydroxy-4-methylhept-2E-enoic acid ethyl ester (922516-84-5) → (2R,3S,4R,6R)-7-(tert-butyldiphenylsilyloxy)-2,3,6-trihydroxy-4-methylheptanoic acid ethyl ester (922516-85-6)

Guidance literature:

With AD-mix-α; methanesulfonamide; In water; tert-butyl alcohol; at 0 ℃; for 18h;

DOI:10.1016/j.tetasy.2006.10.024

Reference yield: 76.0%

(2R,3S,4R,6R)-7-(tert-butyldiphenylsilyloxy)-2,3,6-trihydroxy-4-methylheptanoic acid ethyl ester (922516-85-6) + 2,2-dimethoxy-propane (77-76-9) → (4R,5S)-5-[(2R,4R)-5-(tert-butyldiphenylsilyloxy)-4-hydroxypent-2-yl]-2,2-dimethyl-1,3-dioxolane-4-carboxylic acid ethyl ester (922516-86-7)

Guidance literature:

With 3 A molecular sieve; camphor-10-sulfonic acid; In acetone; at 20 ℃; for 18h;

DOI:10.1016/j.tetasy.2006.10.024

Reference yield:

(2R,3S,4R,6R)-7-(tert-butyldiphenylsilyloxy)-2,3,6-trihydroxy-4-methylheptanoic acid ethyl ester (922516-85-6) → 1-{5-[(2R,4R)-5-(tert-butyldiphenylsilyloxy)-4-(triethylsilyloxy)pent-2-yl]-(4R,5S)-2,2-dimethyl-[1,3]dioxolan-4-yl}-ethanone

Guidance literature:

Multi-step reaction with 5 steps

1: 76 percent / camphorsulfonic acid; molecular sieves 3 Angstroem / acetone / 18 h / 20 °C

2: 97 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 20 °C

3: Me₃SiOK / tetrahydrofuran / 1 h / 20 °C

4: 458 mg / N-methylmorpholine; N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride / CH₂Cl₂ / 18 h / 20 °C

5: 81 percent / tetrahydrofuran; diethyl ether / 1 h / 0 °C

With 4-methyl-morpholine; 2,6-dimethylpyridine; 3 A molecular sieve; camphor-10-sulfonic acid; potassium trimethylsilonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; diethyl ether; dichloromethane; acetone;

DOI:10.1016/j.tetasy.2006.10.024

upstream raw materials:

(4R,6R)-7-(tert-butyldiphenylsilyloxy)-6-hydroxy-4-methylhept-2E-enoic acid ethyl ester

Downstream raw materials:

(4R,5S)-5-[(2R,4R)-5-(tert-butyldiphenylsilyloxy)-4-hydroxypent-2-yl]-2,2-dimethyl-1,3-dioxolane-4-carboxylic acid ethyl ester

(4R,5S)-5-[(2R,4R)-5-(tert-butyldiphenylsilyloxy)-4-(triethylsilyloxy)pent-2-yl]-2,2-dimethyl-1,3-dioxolane-4-carboxylic acid ethyl ester

(4R,5S)-5-[(2R,4R)-5-(tert-butyldiphenylsilyloxy)-4-(triethylsilyloxy)pent-2-yl]-2,2-dimethyl-1,3-dioxolane-4-carboxylic acid N-methoxy-N-methylamide